1-Methylhistidine (BioDeep_00000001240)
Secondary id: BioDeep_00000017774, BioDeep_00000229637, BioDeep_00000268096, BioDeep_00000398042, BioDeep_00000399903, BioDeep_00000400340, BioDeep_00000405182, BioDeep_00000872429
natural product human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite
代谢物信息卡片
化学式: C7H11N3O2 (169.0851226)
中文名称: 3-甲基-L-组氨酸, 1-甲基-L-组氨酸, 1-甲基组氨酸, 3-甲基组氨酸
谱图信息:
最多检出来源 Homo sapiens(blood) 5.69%
Last reviewed on 2024-07-01.
Cite this Page
1-Methylhistidine. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China.
https://query.biodeep.cn/s/1-methylhistidine (retrieved
2024-09-08) (BioDeep RN: BioDeep_00000001240). Licensed
under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).
分子结构信息
SMILES: CN1C=C(CC(N)C(O)=O)N=C1
InChI: InChI=1S/C7H11N3O2/c1-10-3-5(9-4-10)2-6(8)7(11)12/h3-4,6H,2,8H2,1H3,(H,11,12)
描述信息
1-Methylhistidine, also known as 1-MHis or 1MH, belongs to the class of organic compounds known as histidine and derivatives. 1MH is also classified as a methylamino acid. Methylamino acids are primarily proteogenic amino acids (found in proteins) which have been methylated (in situ) on their side chains by various methyltransferase enzymes. Histidine can be methylated at either the N1 or N3 position of its imidazole ring, yielding the isomers 1-methylhistidine (1MH; also referred to as pi-methylhistidine) or 3-methylhistidine (3MH; tau-methylhistidine), respectively. There is considerable confusion with regard to the nomenclature of the methylated nitrogen atoms on the imidazole ring of histidine and other histidine-containing peptides such as anserine. In particular, older literature (mostly prior to the year 2000) designated anserine (Npi methylated) as beta-alanyl-N1-methyl-histidine, whereas according to standard IUPAC nomenclature, anserine is correctly named as beta-alanyl-N3-methyl-histidine. As a result, many papers published prior to the year 2000 incorrectly identified 1MH as a specific marker for dietary consumption or various pathophysiological effects when they really were referring to 3MH (PMID: 24137022). Recent discoveries have shown that 1MH is produced in essentially all mammals (and other vertebrates) via the enzyme known as METTL9 (PMID: 33563959). METTL9 is a broad-specificity methyltransferase that mediates the formation of the majority of 1MH present in mammalian proteomes. METTL9-catalyzed methylation requires a His-x-His (HxH) motif, where "x" is a small amino acid. This HxH motif is found in a number of abundant mammalian proteins such as ARMC6, S100A9, and NDUFB3 (PMID: 33563959). Because of its abundance in many muscle-related proteins, 1MH has been found to be a good biomarker for the consumption of meat (PMID: 21527577). Dietary studies have shown that poultry consumption (p-trend = 0.0006) and chicken consumption (p-trend = 0.0003) are associated with increased levels of 1MH in human plasma (PMID: 30018457). The consumption of fish, especially salmon and cod, has also been shown to increase the levels of 1MH in serum and urine (PMID: 31401679). As a general rule, urinary 1MH is associated with white meat intake (p< 0.001), whereas urinary 3MH is associated with red meat intake (p< 0.001) (PMID: 34091671).
1-Methyl-L-histidine is an objective indicator of meat ingestion and exogenous 3-methylhistidine (3MH) intake.
1-Methyl-L-histidine is an objective indicator of meat ingestion and exogenous 3-methylhistidine (3MH) intake.
3-Methyl-L-histidine is a biomarker for meat consumption, especially chicken. It is also a biomarker for the consumption of soy products.
同义名列表
22 个代谢物同义名
(2S)-2-Amino-3-(1-methyl-1H-imidazol-4-yl)propanoic acid; (2S)-2-Amino-3-(1-methyl-1H-imidazol-4-yl)propanoate; 1-Methylhistidine dihydrochloride; 1-N-Methyl-L-histidine; N1-Methyl-L-histidine; 1-Methyl-L-histidine; 3-Methyl-L-histidine; L-1-Methylhistidine; 1-Methyl-histidine; Pi-methylhistidine; 1-Methyl histidine; H-D-His(tau-Me)-OH; 1-Methylhistidine; 1 Methylhistidine; 1-MHis; 3-(1-Methylimidazol-5-yl)-L-alanine; 1-Methyl-L-histidine (archaic); N(PAI)-METHYL-L-HISTIDINE; π-Methyl-L-histidine; L-3-Methylhistidine; 1-Methylhistidine; 3-Methylhistidine
数据库引用编号
35 个数据库交叉引用编号
- ChEBI: CHEBI:27596
- ChEBI: CHEBI:50599
- KEGG: C01152
- PubChem: 64969
- PubChem: 92105
- HMDB: HMDB0000001
- Metlin: METLIN3293
- DrugBank: DB04151
- ChEMBL: CHEMBL1233327
- Wikipedia: Methylhistidine
- KNApSAcK: C00052105
- foodb: FDB093588
- chemspider: 83153
- CAS: 332-80-9
- CAS: 368-16-1
- MoNA: KO003467
- MoNA: PS096707
- MoNA: PS096702
- MoNA: PS096703
- MoNA: PS096701
- MoNA: PS096704
- MoNA: KO003469
- MoNA: KO003471
- MoNA: PR100835
- MoNA: PS096705
- MoNA: PR100385
- MoNA: KO003468
- MoNA: KO003470
- PMhub: MS000000113
- PDB-CCD: MHS
- 3DMET: B01394
- NIKKAJI: J111.364J
- RefMet: 1-Methylhistidine
- medchemexpress: HY-W017006
- medchemexpress: HY-W017007
分类词条
相关代谢途径
Reactome(0)
BioCyc(0)
PlantCyc(0)
代谢反应
21 个相关的代谢反应过程信息。
Reactome(0)
BioCyc(0)
WikiPathways(0)
Plant Reactome(0)
INOH(0)
PlantCyc(0)
COVID-19 Disease Map(0)
PathBank(21)
- Histidine Metabolism:
-Alanine + Adenosine triphosphate + L-Histidine ⟶ Adenosine diphosphate + Carnosine + Phosphate
- beta-Alanine Metabolism:
1,3-Diaminopropane + Oxygen + Water ⟶ 3-Aminopropionaldehyde + Ammonia + Hydrogen peroxide
- GABA-Transaminase Deficiency:
1,3-Diaminopropane + Oxygen + Water ⟶ 3-Aminopropionaldehyde + Ammonia + Hydrogen peroxide
- Histidinemia:
-Alanine + Adenosine triphosphate + L-Histidine ⟶ Adenosine diphosphate + Carnosine + Phosphate
- Ureidopropionase Deficiency:
1,3-Diaminopropane + Oxygen + Water ⟶ 3-Aminopropionaldehyde + Ammonia + Hydrogen peroxide
- Carnosinuria, Carnosinemia:
1,3-Diaminopropane + Oxygen + Water ⟶ 3-Aminopropionaldehyde + Ammonia + Hydrogen peroxide
- beta-Alanine Metabolism:
1,3-Diaminopropane + Oxygen + Water ⟶ 3-Aminopropionaldehyde + Ammonia + Hydrogen peroxide
- Histidine Metabolism:
Carnosine + Water ⟶ -Alanine + L-Histidine
- GABA-Transaminase Deficiency:
1,3-Diaminopropane + Oxygen + Water ⟶ 3-Aminopropionaldehyde + Ammonia + Hydrogen peroxide
- Histidinemia:
Carnosine + Water ⟶ -Alanine + L-Histidine
- Ureidopropionase Deficiency:
1,3-Diaminopropane + Oxygen + Water ⟶ 3-Aminopropionaldehyde + Ammonia + Hydrogen peroxide
- Carnosinuria, Carnosinemia:
1,3-Diaminopropane + Oxygen + Water ⟶ 3-Aminopropionaldehyde + Ammonia + Hydrogen peroxide
- beta-Alanine Metabolism:
1,3-Diaminopropane + Oxygen + Water ⟶ 3-Aminopropionaldehyde + Ammonia + Hydrogen peroxide
- Histidine Metabolism:
Carnosine + Water ⟶ -Alanine + L-Histidine
- beta-Alanine Metabolism:
1,3-Diaminopropane + Oxygen + Water ⟶ 3-Aminopropionaldehyde + Ammonia + Hydrogen peroxide
- Histidine Metabolism:
Carnosine + Water ⟶ -Alanine + L-Histidine
- beta-Alanine Metabolism:
1,3-Diaminopropane + Oxygen + Water ⟶ 3-Aminopropionaldehyde + Ammonia + Hydrogen peroxide
- beta-Alanine Metabolism:
1,3-Diaminopropane + Oxygen + Water ⟶ 3-Aminopropionaldehyde + Ammonia + Hydrogen peroxide
- GABA-Transaminase Deficiency:
1,3-Diaminopropane + Oxygen + Water ⟶ 3-Aminopropionaldehyde + Ammonia + Hydrogen peroxide
- Histidinemia:
Carnosine + Water ⟶ -Alanine + L-Histidine
- Carnosinuria, Carnosinemia:
1,3-Diaminopropane + Oxygen + Water ⟶ 3-Aminopropionaldehyde + Ammonia + Hydrogen peroxide
PharmGKB(0)
2 个相关的物种来源信息
- 9606 Homo sapiens: -
- 569774 金线莲: -
在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有:
- PubMed: 来源于PubMed文献库中的文献信息,我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表,这个列表按照代谢物同时出现的文献数量降序排序,取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
- NCBI Taxonomy: 通过文献数据挖掘,得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序,取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
- Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
- Chemical Reaction: 在化学反应过程中,存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。
点击图上的相关代谢物的名称,可以跳转到相关代谢物的信息页面。
文献列表
- M Yusof Said, Angelica Rodriguez-Niño, Adrian Post, Joelle C Schutten, Lyanne M Kieneker, Antonio W Gomes-Neto, Marco van Londen, Maryse Cj Osté, Karin J Borgonjen-van den Berg, Ilja M Nolte, Else van den Berg, Pim de Blaauw, Jennifer van der Krogt, M Rebecca Heiner-Fokkema, Gerjan Navis, Benito A Yard, Stephan Jl Bakker. Meat intake and risk of mortality and graft failure in kidney transplant recipients.
The American journal of clinical nutrition.
2021 10; 114(4):1505-1517. doi:
10.1093/ajcn/nqab185
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The journal of trauma and acute care surgery.
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10.1097/ta.0000000000003285
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Journal of hypertension.
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Transplantation proceedings.
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Journal of dairy science.
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European journal of nutrition.
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Nutrients.
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American journal of physiology. Cell physiology.
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European journal of clinical nutrition.
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The Journal of nutritional biochemistry.
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2018 09; 17(9):3184-3194. doi:
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Journal of agricultural and food chemistry.
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Scientific reports.
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Molecular nutrition & food research.
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JPEN. Journal of parenteral and enteral nutrition.
2018 02; 42(2):361-370. doi:
10.1177/0148607116678831
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The Journal of nutrition.
2017 Oct; 147(10):1850-1857. doi:
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Journal of chromatography. A.
2017 Sep; 1517(?):66-78. doi:
10.1016/j.chroma.2017.08.024
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American journal of veterinary research.
2017 Jun; 78(6):735-744. doi:
10.2460/ajvr.78.6.735
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Journal of dairy science.
2017 Jun; 100(6):4528-4538. doi:
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. [PMID: 28434720] - Liufeng Zheng, Fangrui Zuo, Shengjun Zhao, Pingli He, Hongkui Wei, Quanhang Xiang, Jiaman Pang, Jian Peng. Dietary supplementation of branched-chain amino acids increases muscle net amino acid fluxes through elevating their substrate availability and intramuscular catabolism in young pigs.
The British journal of nutrition.
2017 Apr; 117(7):911-922. doi:
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Nutrients.
2016 Dec; 9(1):. doi:
10.3390/nu9010010
. [PMID: 28036059] - Yuki Iida, Takenori Yamazaki, Hajime Arima, Tsutomu Kawabe, Sumio Yamada. Predictors of surgery-induced muscle proteolysis in patients undergoing cardiac surgery.
Journal of cardiology.
2016 12; 68(6):536-541. doi:
10.1016/j.jjcc.2015.11.011
. [PMID: 26777625] - Saki Shimamoto, Daichi Ijiri, Kazuki Nakashima, Mana Kawaguchi, Yoshitaka Ishimaru, Airi Furukawa, Akira Ohtsuka. Clenbuterol changes phosphorylated FOXO1 localization and decreases protein degradation in the sartorius muscle of neonatal chicks.
Bioscience, biotechnology, and biochemistry.
2016 Aug; 80(8):1499-504. doi:
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Molecular nutrition & food research.
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General and comparative endocrinology.
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The Journal of nutrition.
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2016 Feb; 99(2):1145-1160. doi:
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Journal of animal science.
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International journal of psychiatry in clinical practice.
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Pediatric critical care medicine : a journal of the Society of Critical Care Medicine and the World Federation of Pediatric Intensive and Critical Care Societies.
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Journal of dairy science.
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. [PMID: 25841896] - Takeki Uehara, Akira Horinouchi, Yuji Morikawa, Yutaka Tonomura, Keiichi Minami, Atsushi Ono, Jyoji Yamate, Hiroshi Yamada, Yasuo Ohno, Tetsuro Urushidani. Identification of metabolomic biomarkers for drug-induced acute kidney injury in rats.
Journal of applied toxicology : JAT.
2014 Oct; 34(10):1087-95. doi:
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. [PMID: 24114878] - Amanda J Cross, Jacqueline M Major, Nathaniel Rothman, Rashmi Sinha. Urinary 1-methylhistidine and 3-methylhistidine, meat intake, and colorectal adenoma risk.
European journal of cancer prevention : the official journal of the European Cancer Prevention Organisation (ECP).
2014 Sep; 23(5):385-90. doi:
10.1097/cej.0000000000000027
. [PMID: 24681531] - N Kambe, K Tanaka, N Kakuta, R Kawanishi, Y M Tsutsumi. The influence of glucose load on metabolism during minor surgery using remifentanil-induced anesthesia.
Acta anaesthesiologica Scandinavica.
2014 Sep; 58(8):948-54. doi:
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Nutrition (Burbank, Los Angeles County, Calif.).
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European journal of nutrition.
2014 Feb; 53(1):61-71. doi:
10.1007/s00394-013-0498-6
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Asia Pacific journal of clinical nutrition.
2014; 23(3):400-7. doi:
10.6133/apjcn.2014.23.3.10
. [PMID: 25164450] - J A A Pires, C Delavaud, Y Faulconnier, D Pomiès, Y Chilliard. Effects of body condition score at calving on indicators of fat and protein mobilization of periparturient Holstein-Friesian cows.
Journal of dairy science.
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